Yellow pyrazolone dye for wool.



UNITED STATES PATENT 1C.

HUGO GELDERMANN, OF GROSS-LICHTERFELDE-OST, GERMANY, ASSIGNOR TO ACTIEN GESELLSCHAFT FIIR ANILIN FABRIKATION, OFv BERLIN, GERMANY.

No Drawing.

Specification of Letters Patent,

Patented Jan. 17, 1911.

Application filed September 26, 1910. Serial No. 583,870.

T 0 all whom it may concern:

Be it known that I, HUGO GELDERMANN, a subject of the Kin of Prussia, residing at Gross-Lich'tcrfolde-6st, Germany, (my postofice address being Grabenstrasse 12, Gross- Lichterfelde-Ost, Germany,) have invented certain new and useful Improvements in Yellow Dyes for Wool, of which the following is a specification.

My presentinvention relates to a new and very valuable dyestutl which dyes wool without. a mordant from an acid bath clear and intense yellow tints of a very good fastness. This coloring matter contains a pyrazolone nucleus and possesses the "following constitution:

The new d yestufl' ma y be produced by diazotizing ortho-chloroanilin and combining the diazo compound thus obtained with orthochloro-l-pl1enyl-3met.hyl-o-pyrazolone-metasulfonic acid.

The following example serves to illustrate my invention, the parts being by weight. 12.5 parts of ortho-chloroanilin are diazotized in the usual manner by means of hydrochloric acid and sodium nitrite; the diazo compound thusobtainr-d is combined with 3L5 parts of the sodium salt of the above cited ortho-chloro-l-phenyl-l-methyl-S-pyrazolonemeta-sulfonic acid in the presence of such a quantity of sodium carbonate as will guar untce an alkaline reaction throughout the combination process. The reaction being finished, the dycstuli is isolated in the usual manner by means of common salt; it. pro duccs on wool from an acid hath clear and intense yellow tints. The new dyostutt' thus produced forms after drying and pulverizing a yellow powder which dissolves in water and in alcohol to a yellow solution. This aqueous solution on addition ol concentrated hydrochloric acid st'fpilltlith' the free acid of the dyestnfl in the shape of light yellow flakes. whereas by the addition of concentratcd liquor aunnonizn or concentrated sodalye the coloration of the solution is only very little changed, the solution assuming a more reddish tint. The neutral aqueous solution when boiled with zinc dust is decolorized, but by the oxidizing action of the air assumes afterward a violet color. The new coloring matter dissolves in concentrated sulfuric acid to a yellow solution which on the addition of ice separates light yellow flakes.

My present invention is not limited to the foregoing example or to the details given therein. I wish particularly to state that instead of using a component containing the pyrazolone nucleus already formed in manufactnring the dye one can form this nucleus in the second or third step ofthe production of the dyestufl'; thus I may combine the diazo compound of ortho-chloroanilin with acetacetio ether and condense the product thus obtained with ortho-ehlorophenylhydrazin-meta-sulfonic acid to the corresponding pyrazolone derivative. Or I may condense ortho-chloro phenylhydrazin meta sulfonic acid with acetacetic ether to the corresponding h'yd'razone, then combine this hydrazone with the diazo compound of ortho-chloroanilin to form the corresponding dye compound and finally form the pyrazolone nucleus by the action of a suitable condensing agent.

Having now described the invention and the manner in which it may be performed what I claim is,

As a new article of manufacture the new yellow dye for wool having the formula:

ton; this new dyestuii in the sha e of the dr sodium salt when pulverized orining a e low powder, which dissolves in water an in alcohol to a yellow solution, and this aqueous solution on the addition of concentrated hydrochloric acid separating the free acid of the dyestufi' in the shape of light yellow flakes, whereas by the addition of concentrated liquor ammonia: or concentrated soda lye the coloration becomes only very little more reddish and the neutral aqueous solution when boiled with zinc dust being decolorized, but by the oxidizing action of .the air assuming afterward a violet color, which new coloring matter dissolves in concenmy hand in presence of two subscribing-wittrated sulfuric acid tofu yellow sol111ti })ln nesses.- which on the addition 0 ice se arates ig t yellow flakes, and thisnew d g estufi' ,pro- HUGO GELDERMANN' 5 ducing on wool from an acid b'ath clear and Witnesses:

intense yellow tints of a very good fastness. J HENRY HASPER,

In testimony whereof I have hereunto'set QWOLDEMAR HAUPT. 

